Sodium Hydroxide → 3-(Methylamino)propanoic acid, N-BOC protected

HRID 426031Notes

Reaction equation

HRID 426031 reaction equation
[OH-].[Na+].[C:3]([O:7][C:8]([N:10]([CH3:18])[CH2:11][CH2:12][C:13]([O:15]CC)=[O:14])=[O:9])([CH3:6])([CH3:5])[CH3:4]>C1COCC1.CCO.O>[C:3]([O:7][C:8]([N:10]([CH3:18])[CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[O:9])([CH3:6])([CH3:5])[CH3:4]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 13896291ethyl 3-(N-Boc-N-methylamino)propionate

Product 1

HCID 27609523-(Methylamino)propanoic acid, N-BOC protectedYield 73.2%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of sodium hydroxide (112 g, 2.8 mol) in THF (1200 mL) and EtOH (1800 mL) was added ethyl 3-(tert-butoxycarbonyl(methyl)amino)propanoate (300 g, 1.4 mol). The resulting mixture was stirred for 3 h. The mixture was diluted with water (1000 mL) and evaporated to remove volatiles. The water phase was washed with CH2Cl2 (800 mL×3). The inorganic layer was cooled in an ice bath and acidified with 1 N HCl until the pH was adjusted to 1-2. CH2Cl2 (1000 mL×4) was quickly added to extract the product acid. The organic phase was dried over anhydrous Na2SO4 and concentrated to give 3-(tert-butoxycarbonyl(methyl)amino)propanoic acid (208 g, 73.2%) as oil, which was used in the next step without further purification.

Workup

  1. customevaporated
  2. customto remove volatiles
  3. washThe water phase was washed with CH2Cl2 (800 mL×3)
  4. temperatureThe inorganic layer was cooled in an ice bath
  5. additionCH2Cl2 (1000 mL×4) was quickly added
  6. extractionto extract the product acid
  7. dry with materialThe organic phase was dried over anhydrous Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-555aec463f584a839769c8137853e527
Source dataset
uspto-grants-2012_01
Patent number
US08106221B2

Reaction notes

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